CZ295578B6 - Modifikovaná forma hydrochloridu R(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipekotové kyseliny, způsob její přípravy a použití a farmaceutické prostředky ji obsahující - Google Patents

Modifikovaná forma hydrochloridu R(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipekotové kyseliny, způsob její přípravy a použití a farmaceutické prostředky ji obsahující Download PDF

Info

Publication number: CZ295578B6
Authority: CZ; Czechia
Prior art keywords: methylthien; crystalline form; enyl; acid hydrochloride; anhydrous crystalline
Prior art date: 1996-06-14

Application number

CZ19984019A

Other languages

Czech (cs)

English (en)

Other versions

CZ401998A3 (cs

Inventor

Preben Ahrndt

Henning Borge Petersen

Vincent H. Chang

Kimberly Ann Allen

Michael H. Chain

Original Assignee

Novo Nordisk A/S

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-06-14

Filing date

1997-06-03

Publication date

2005-08-17

1997-06-03 Application filed by Novo Nordisk A/S filed Critical Novo Nordisk A/S

1999-06-16 Publication of CZ401998A3 publication Critical patent/CZ401998A3/cs

2005-08-17 Publication of CZ295578B6 publication Critical patent/CZ295578B6/cs

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title abstract description 6
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 11
229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 10
201000010099 disease Diseases 0.000 claims abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
206010015037 epilepsy Diseases 0.000 claims abstract description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
229960002410 tiagabine hydrochloride Drugs 0.000 claims description 19
YUKARLAABCGMCN-PKLMIRHRSA-N tiagabine hydrochloride Chemical compound Cl.C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C YUKARLAABCGMCN-PKLMIRHRSA-N 0.000 claims description 19
238000010521 absorption reaction Methods 0.000 claims description 9
-1 3-methylthien-2-yl Chemical group 0.000 claims description 7
LRZWUDOLANRDSF-NUBCRITNSA-N (3r)-piperidine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H]1CCCNC1 LRZWUDOLANRDSF-NUBCRITNSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims description 2
238000004090 dissolution Methods 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
230000001376 precipitating effect Effects 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 12
239000000047 product Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 5
KOZCGZMZXXVHCF-GGMCWBHBSA-N (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid hydrate hydrochloride Chemical compound O.Cl.C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C KOZCGZMZXXVHCF-GGMCWBHBSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
150000004682 monohydrates Chemical class 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
239000011230 binding agent Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
NSGCWILIYQUGIO-GOSISDBHSA-N ethyl (3r)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylate Chemical compound C1[C@H](C(=O)OCC)CCCN1CCC=C(C1=C(C=CS1)C)C1=C(C)C=CS1 NSGCWILIYQUGIO-GOSISDBHSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002411 thermogravimetry Methods 0.000 description 2
229960001918 tiagabine Drugs 0.000 description 2
PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 2
WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229940066595 beta tocopherol Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940127554 medical product Drugs 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011590 β-tocopherol Substances 0.000 description 1
235000007680 β-tocopherol Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)

CZ19984019A 1996-06-14 1997-06-03 Modifikovaná forma hydrochloridu R(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipekotové kyseliny, způsob její přípravy a použití a farmaceutické prostředky ji obsahující CZ295578B6 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK66196		1996-06-14

Publications (2)

Publication Number	Publication Date
CZ401998A3 CZ401998A3 (cs)	1999-06-16
CZ295578B6 true CZ295578B6 (cs)	2005-08-17

Family

ID=8096101

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ19984019A CZ295578B6 (cs)	1996-06-14	1997-06-03	Modifikovaná forma hydrochloridu R(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipekotové kyseliny, způsob její přípravy a použití a farmaceutické prostředky ji obsahující

Country Status (20)

Country	Link
EP (1)	EP0906309B1 (de)
JP (1)	JP2000511909A (de)
CN (1)	CN1636565A (de)
AR (1)	AR008236A1 (de)
AT (1)	ATE223405T1 (de)
AU (1)	AU723267B2 (de)
BR (1)	BR9709725A (de)
CZ (1)	CZ295578B6 (de)
DE (1)	DE69715196T2 (de)
DK (1)	DK0906309T3 (de)
ES (1)	ES2181002T3 (de)
HU (1)	HUP9904035A3 (de)
IL (1)	IL127469A (de)
NO (1)	NO316889B1 (de)
PL (1)	PL190858B1 (de)
PT (1)	PT906309E (de)
RU (1)	RU2177478C2 (de)
UA (1)	UA52661C2 (de)
WO (1)	WO1997047619A1 (de)
ZA (1)	ZA975266B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5914333A (en) *	1996-07-31	1999-06-22	Novo Nordisk A/S	Treatment of psychotic disorders
IE970588A1 (en)	1997-08-01	2000-08-23	Elan Corp Plc	Controlled release pharmaceutical compositions containing tiagabine
PT991409E (pt) *	1997-08-01	2002-06-28	Elan Corp Plc	Composicoes farmaceuticas de libertacao controlada contendo tiagabina
CN1314684C (zh) *	2003-12-24	2007-05-09	中国科学院上海有机化学研究所	噻加宾及其消旋体和s－构型的合成方法及其无定形粉末的制法
GB0402118D0 (en) *	2004-01-30	2004-03-03	Merck Sharp & Dohme	Polymorphic forms of a GABAA agonist
WO2005092886A1 (en) *	2004-03-29	2005-10-06	Ranbaxy Laboratories Limited	Process for the preparation of amorphous form of tiagabine
US20080064727A1 (en) *	2006-08-18	2008-03-13	Cephalon, Inc.	Crystalline forms of tiagabine hydrochloride

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK288385D0 (da) *	1985-06-26	1985-06-26	Novo Industri As	Aminosyrederivater
DK58291D0 (da) *	1991-04-02	1991-04-02	Novo Nordisk As	Krystalinsk stof og dets fremstilling
US5750140A (en) *	1994-05-20	1998-05-12	Novo Nordisk A/S	Transdermal delivery of tiagabine

1997
- 1997-03-06 UA UA98126589A patent/UA52661C2/uk unknown
- 1997-06-03 BR BR9709725A patent/BR9709725A/pt not_active IP Right Cessation
- 1997-06-03 AT AT97927006T patent/ATE223405T1/de active
- 1997-06-03 PT PT97927006T patent/PT906309E/pt unknown
- 1997-06-03 DK DK97927006T patent/DK0906309T3/da active
- 1997-06-03 PL PL330424A patent/PL190858B1/pl unknown
- 1997-06-03 IL IL12746997A patent/IL127469A/xx not_active IP Right Cessation
- 1997-06-03 CZ CZ19984019A patent/CZ295578B6/cs not_active IP Right Cessation
- 1997-06-03 CN CNA2004100926232A patent/CN1636565A/zh active Pending
- 1997-06-03 DE DE69715196T patent/DE69715196T2/de not_active Expired - Lifetime
- 1997-06-03 HU HU9904035A patent/HUP9904035A3/hu unknown
- 1997-06-03 AU AU31653/97A patent/AU723267B2/en not_active Expired
- 1997-06-03 RU RU99100703/04A patent/RU2177478C2/ru not_active IP Right Cessation
- 1997-06-03 EP EP97927006A patent/EP0906309B1/de not_active Expired - Lifetime
- 1997-06-03 JP JP10501077A patent/JP2000511909A/ja not_active Ceased
- 1997-06-03 ES ES97927006T patent/ES2181002T3/es not_active Expired - Lifetime
- 1997-06-03 WO PCT/DK1997/000244 patent/WO1997047619A1/en not_active Ceased
- 1997-06-13 AR ARP970102614A patent/AR008236A1/es active IP Right Grant
- 1997-06-13 ZA ZA9705266A patent/ZA975266B/xx unknown
1998
- 1998-12-11 NO NO19985809A patent/NO316889B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP9904035A3 (en)	2000-07-28
AU723267B2 (en)	2000-08-24
UA52661C2 (uk)	2003-01-15
IL127469A (en)	2001-01-11
HUP9904035A2 (hu)	2000-05-28
WO1997047619A1 (en)	1997-12-18
CN1636565A (zh)	2005-07-13
DE69715196D1 (de)	2002-10-10
PT906309E (pt)	2002-12-31
DK0906309T3 (da)	2002-12-16
ATE223405T1 (de)	2002-09-15
RU2177478C2 (ru)	2001-12-27
ZA975266B (en)	1998-02-04
PL330424A1 (en)	1999-05-10
AU3165397A (en)	1998-01-07
EP0906309A1 (de)	1999-04-07
ES2181002T3 (es)	2003-02-16
JP2000511909A (ja)	2000-09-12
BR9709725A (pt)	1999-08-10
CZ401998A3 (cs)	1999-06-16
NO316889B1 (no)	2004-06-14
EP0906309B1 (de)	2002-09-04
PL190858B1 (pl)	2006-02-28
NO985809L (no)	1998-12-11
NO985809D0 (no)	1998-12-11
DE69715196T2 (de)	2003-05-15
IL127469A0 (en)	1999-10-28
AR008236A1 (es)	1999-12-29

Legal Events

Date	Code	Title	Description
2000-06-30	PD00	Pending as of 2000-06-30 in czech republic
2017-06-14	MK4A	Patent expired	Effective date: 20170603

Publication	Publication Date	Title
US5958951A (en)	1999-09-28	Modified form of the R(-)-N-(4,4-di(3-methylthien-2-yl)but-3-enyl)-nipecotic acid hydrochloride
SK167698A3 (en)	1999-06-11	Polymorphs of donepezil hydrochloride and process for production
EP0579681B1 (de)	1999-06-02	Kristallines tiagabinehydrochlorid-monohydrat, seine herstellung und verwendung
CZ289730B6 (cs)	2002-03-13	Krystalický hydrochlorid (R)-(-)-2-{N-[4-(1,1-dioxido-3-oxo-2,3-dihydrobenzisothiazol-2-yl)-budyl]-aminomethyl}-chromanu, způsob jeho výroby, farmaceutický prostředek tuto látku obsahující a její pouľití
EP0906309B1 (de)	2002-09-04	Modifizierte form des hydrochlorids der r(-)-n-(4,4-di(-3-methylthien-2-yl)but-3-enyl)-nipecotinsäure
EP0703915B1 (de)	2000-09-27	Xamonelin-Tartrat
BE1014454A6 (nl)	2003-10-07	Amlodipinehemimaleaat.
US7335380B2 (en)	2008-02-26	Amlodipine free base
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